


A Night with the Ilithid

by ImSpooped



Category: Critical Role (Web Series), Dungeons & Dragons (Roleplaying Game)
Genre: Anal Sex, Campaign 1 (Critical Role), F/M, Ilithid, Oral Sex, Set during Episode 8, Vaginal Sex, Yall fuck and thats it lol, mind flayer - Freeform, reader is female, you've seen enough hentai to know what's about to happen
Language: English
Status: Completed
Published: 2018-09-27
Updated: 2018-09-27
Packaged: 2019-07-18 08:19:01
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,983
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16114502
Author URL: https://archiveofourown.org/users/ImSpooped/pseuds/ImSpooped
Summary: Instead of Lady Kima, you take the first night watch with Clarota while the rest of Vox Machina sleeps. Let's just say you... have a thing for mind flayers, and are quick to make your move.





	A Night with the Ilithid

Smooth purple skin, a deep sultry voice that rumbled in your mind, and oh _yes_ those tentacles.

You take in the form of the creature in front of you. Vex and Keyleth introduce him as Clarota, an Ilithid outcast from his hive. They say he is willing to work with Vox Machina as an ally while in these caves.

Your party members raise arms as the see him, but not you. You trust Vex and Keyleth’s judgement in bringing him along to meet everyone else. Plus he’s hot.

Fast forward a few days and few battles, and Vox Machina has at last found Lady Kima, who absolutely _detests_ the thought of being allies with Clarota. When everyone is picking sides, you choose him. If Grog chooses Kima with his _other_ head, then you’ll choose Clarota for the same reason. Thankfully, no one asks for your motivation behind your decision.

After a tense discussion and lots of persuading, Clarota and Lady Kima…. Agree to travel together.

After further adventuring into the cave system and several battles, Clarota and Kima come to... a mutual agreement. If you can call it that. They both share their doubts about the other but it isn't as tense.  
  
Finally, it is nighttime. Well, you don't know that for sure, since there is no natural light to tell the time of day by, but everyone agrees that it is time to sleep.

“Lady Kima, Clarota, may I suggest you take the first watch?” Vax asks. Kima and Clarota don't need as much sleep as everyone else, so they agree to take a shift keeping guard. Similarly, you and Pike don't need as much rest, so you two will be taking the second shift.   
  
As you're finishing taking stock of your gear and ready to lie down and sleep, you hear the men of your group gossiping about Kima and Clarota.  "Oh my god what if they start fucking?” Scanlan blurts out, making everyone burst out in laughter.

“So it’s going to be that sort of evening, excellent,” Percy adds in with sarcasm in his voice.   
  
Oh no. That's right. The tension between them, an agreement not to kill each other, the privacy of being the only ones awake, plus nothing better to do while keeping guard? Oh my god, what if they fuck!!?!   
  
You begin to panic. As improbable as it is, you can't let Kima and Clarota... have the opportunity.   
  
You were also... kind of miffed. If anyone was interested in Clarota, it was you. The fact that the guys weren't gossiping about you and Clarota kinda made you jealous. You had flirted with Clarota at any given opportunity, winking at him while making some risqué remarks. You swear you saw him blush when you said you wanted to 'see what them tentacles do'.   
  
Thinking quickly, you stride over to Kima. Thankfully, Pike is with her.   
  
"Kima, I'm feeling a bit restless, would you mind swapping shifts with me?" You ask her politely, looking at Pike too. Pike smiles at you, a silent way of saying she doesn't mind her guard shift being with Kima instead of you.   
  
"Oh switch?" Kima pauses, thinking. "Aye, that will do fine. I could use my rest right now. Also saves me from being alone with that thing."  
  
"Great, goodnight then you two." You wave bye to Pike and Kima, smiling more than you should have.   
  
Crossing your camp, you grab your thickest fur to lay on and quickly join Clarota at the sentry station. He's sitting in a meditative position, eyes closed and still levitating about a foot above the ground.   
  
Approaching from his right side, you greet him. "Hope it won't be a bother, but Lady Kima and I are swapping shifts for the night. Just you and me now." You throw in a sexy wink, but with his eyes being closed, Clarota didn't notice. You let out a small huff of annoyance on accident.   
  
And OF COURSE he notices the huff, and with that he opens his eyes.  
  
"Does this perturb you? You seem put off by my company?" He asks, eyes locked on to yours, but facing forward still.   
  
"Quite the opposite really. I've been wanting some alone time with you," you say as you unroll your fur and join him on the ground. "Actually, I asked Lady Kima to swap shifts with me so I could actually have that alone time."  
  
Clarota turns to face you now, maintaining eye contact, his gaze intensifying.  "Should I take that as a threat or a compliment?" His tentacles begin to writhe, gliding along one another in anticipation.   
  
You let out a seductive laugh, shrugging off your pack and setting your weapon behind you to make it easier to sit.

Your legs out to your side, you sit propped up on one arm, giving him a devilish smirk. "Now Clarota, you know I've been a big fan of you ever since Vex and Keyleth air lifted you out of that tunnel." With that you rest your free hand just above his knee, hoping he doesn't mind the contact. 

  
Tentacles moving slightly faster now, Clarota ends his levitation. "This 'alone time' you wanted so badly, what were you hoping to get out of it?"   
  
You inhale deeply, giving his thigh a squeeze and sliding your hand further up. "I was... hoping that I could see what you eat besides brains." You threw in another sexy wink, this one actually being seen.    
  
This time his tentacles still, and his eyes focus on your lips as you give them a subtle lick. You smile as you catch him continually looking lower from there, at your ample bosom.    
  
"You risk being caught by your allies, or worse, an enemy, to spend a night with me?" His voice sounds suspicious of you. "How do I know they didn't send you to assassinate me? Be a distraction so the rogue could take me out?"  
  
"Or how am I to know that I won't end up with a hole in my skull? How can I trust you won't do that to me while we're all alone, and then continue your buffet on everyone else while they sleep?" you counter. Maybe that was a bit too rough. "Guess that's why we're allies."  
  
A tense moment passes and you remove your hand from Clarota's leg, but as you're withdrawing your hand, he grips your wrist and pulls you toward him. He has risen to his knees and is now looking over you. He stares at you, his eyes transfixed onto yours, and you can't tell if it's a look of anger or not.   
  
"If you wish for me to stop, then you need but to say so," he says in a neutral tone as he moves himself over you.   
  
You lean back, holding yourself up on your elbows as thick ropey tentacles make their way to your neck, massaging and squirming in a pleasurable way. You let a quiet moan out as his toothy maw rasps at your sensitive neck, goose bumps shooting down your body.  
  
The ministrations on your neck continue as Clarota comes to cup your breasts. "Shall we move forward?" He asks, undoing just one button of your top.   
  
"Y-yes, please," you try not to sound like you're begging.   
  
Your top is quickly unfastened and removed, exposing your chest. Tentacles moves from your neck to your chest, wrapping around your breasts, cupping and massaging them, and the toothy mouth focuses on your right nipple.   
  
You gasp in pain as your bud is pinched too hard, only to moan a second later as the pain transforms into pleasure, the Ilithid now sucking, teeth moved into a gentler position.   
  
You let your head roll back as Clarota continues licking and sucking on your nipples. For a moment you pause to lay down, freeing your arms. With one hand you rub his arm and shoulder, his skin smooth and silky. Your other hand caresses his head, the metal helmet cool to the touch.   
  
And suddenly his mouth is off your chest, he wrenches you away from his helmet. "Touch that again and our alliance may be reconsidered," his angered voice hisses in your mind. "You forget that this helmet is my only protection from the Elder Brain."   
  
"I'm sorry, I wasn't going to take it off of you," you apologize and he releases his grip on your wrist. "I was so distracted by how amazing you were making me feel that I touched it absentmindedly."  
  
"Do it again and you'll be 'absent minded' for a different reason," he threatens, but returns his attention back to your breasts. You swear you heard him chuckle when he said that.   
  
"Was that a pun? I thought you hated puns."  
  
"I do hate puns. Don't insinuate that I would ever make a pun," he snaps at you, all the while pulling your knees apart and settling in between them. You feel his erection pressing against you through your clothing.   
  
"What if I do though? Would you have to PUNish me?"    
  
Oh he did not like that. He lifts into and standing position, pulling you up to your knees as he does so. 

"You will be silenced until that mouth of yours is done saying puns," he growls and removes his clothing, freeing his cock.  
  
His cock is the same light purple as the rest of his skin and only half hard. Below, his heavy balls hang, engorged with arousal.   
  
Before you can get more acquainted with the sight of his cock, he's pulling you closer, tip pushing against your lips.  
  
You gingerly take the head in your mouth, swirling your tongue around it. His cock slowly hardens and grows in size as you take in all that you can.   
  
Once fully erect, you give his cock a few pumps with your mouth before pulling back to admire his member.   
  
He looks to be a very satisfying 7 inches long, maybe more, with a deliciously wide girth that you can't wait to wedge inside you. His head is wide as well, flaring out into a bell shape.   
  
His cock pulses as you look at it, a small bead of pre-cum starting to leak out. You wrap one hand around his shaft, slowly pumping it as you dip down to lick his balls. You take one ball into your mouth, giving it a light suck as you swirl your tongue around it. Clarota gives off a moan that he quickly covers with a hand.   
  
You continue licking and sucking on his balls while continuing to slowly work his cock with your hand. Occasionally you move your mouth to his cockhead, taking in only the tip and licking it thoroughly before returning to his balls. His moans become a little louder each time you switch between his balls and his head, until his hand is no longer able to muffle his sounds.   
  
At that point you release his shaft, instead opting to cup his balls and massage them with one hand. You then take as much of his leaking member into your mouth has you can. Your free hand covers the length that isn't in your mouth.   
  
As you work him with your mouth, his pre-cum is almost flowing freely. It's like an aphrodisiac, making you moan as you taste it. Clarota grips onto your head, holding you still has he fucks your mouth. Your hands move to allow him movement, so you toy with your clit.  
  
As his pumps become faster and lose their rhythm, you know he's close. You eagerly let out moans, begging him to cum down your throat.   
  
"Release me, or I shall finish," he warns, pushing you away.   
  
You refuse, sucking hard on his cock and swirling your tongue around his tip. He grunts as he tries to hold off, breathing heavy and unsteady.   
  
"F-fuck, ah," he grunts, now pulling your head onto his cock, fully fucking your mouth as he releases his seed into the back of your throat. You swallow around him, rubbing your clit recklessly.  
  
"Gah, ah, look what you've done now," he pants, thrusting into your mouth a few last times before slowly pulling out. His tone was scolding but his expression is praising.  
  
"Don't think I'm done with you, mister," you say as you tug off your trousers and lay back on your fur mat. "As I said a few days ago, 'show me what them tentacles do'".   
  
He rolls he eyes at your wording but doesn't hesitate to kneel down and pull your knees apart.  
  
He begins by rubbing up and down your vulva with his thumb. He chuckles, impressed by how extremely soaked you are. Satisfied, he leaves his thumb on your clit, pressing on in rhythmically. One tentacle rubs up against your wetness, coating itself in slick.   
  
"Yes... ah yes, that's good," you moan as the tentacle prods at your entrance. It slowly enters, filling you. "Clarota, oh you’re so good, it's been so long for me..." You babble, enjoying the feeling of a thick tentacle fuck you.  
  
The combination of being filled over and over and the pressure on your clit soon has you nearing an orgasm. Your feet scramble, trying to find the best resting place to ride out your climax. Breath hastening, you moan for Clarota to continue, but are very displeased to find him withdrawing from you.   
  
You frown, about to mouth off to him with you feel a nudge at your ass. The tentacle that is slick with your wetness is slowly making its way into your ass, exiting new nerve endings.   
  
It pushes in, stretching you a pleasurable amount, and it begins to wriggle. The sensation is new to you, frightening almost, but he’s taking it slow.

“Y’know, I was gonna ask you something,” you say in an attempt to calm yourself, “IF you got to/had to eat one of our brains, whose would you choose?”

The Ilithid huffs, almost stopping his ministrations. He gives you a look that says ‘Don’t ask me anymore dumb questions or we’re stopping’. You allow the question to go unanswered.

He rewards you by inserting a second tentacle, your ass and pussy both now occupied.

You feel a familiar buildup in your abdomen, one that you hadn’t experience in quiet a long time. You bite your lip and groan, hoping that he actually lets you cum this time.

“D-don’t stop, okay?” you stutter, almost reaching down to push his head against you, but instead grip at the soft pet underneath you. “Fuck…Fuck Clarota, I’m gonna cum, please let me cum,” you beg. A purple hand moves up to rub your clit and causes your vision to go white. You bite your hand to silence yourself as your body tenses and you soak up ever bit of pleasure he’s giving you. You feel him struggle to keep his tentacles inside as both of your holes pulse and squeeze around him.

Sighing contentedly, you relax on your pelt, patting the space next to you for Clarota to lay on.

“Oh?” he says, rising to his knees, giving you an amused look, “Did you think we were finished?”

Looking down, you see his cock is hard and ready to go again. Already, he’s spreading your legs, lining himself up. You feel his head rub up and down your slick several times, bumping your overstimulated clit.

“H-hey, slow down, I’m still overstimulated,” you whimper.

He obliges, leaning forward to suck and pinch on your nipples again. His cock is still rubbing against you, and it becomes more pleasurable as you come down from your first orgasm. After a few minutes of his massage, you position your hips to a better angle, and he takes that as his cue, guiding his cock to your entrance and pushing the head in.

“Ah—fuck!” you catch yourself in time to not actually scream that out. The incredible girth of his cock catches you off guard. He slowly sheathes himself inside you, covering your mouth with his hand. He stills, letting you adjust to being filled so much. As he does this, he suckles on your neck and slowly rubs your clit.

“Very good,” his voice rumbles sexily in your head. “You’re taking this cock so well. Your pussy feels so warm and tight around me. I’m going to start moving now.”

As promised, he pulls out slowly and inserts himself at an even more excruciatingly slow speed. You moan against his hand and your eyes are rolling back in your head as his cock stretches you again.

Several slow pumps later and you’re craving more. Once Clarota has almost fully pulled out, you wrap your legs around him and force him to quickly pound back into you.

He hisses and bites down on your neck, teeth made to bore through bone now rasping harshly at your flesh. Unable to speak through his hand, you push him away by his shoulders. You can see you blood on his teeth and tentacles.

“Forgive me,” he pants, taking a moment to examine your injury. “The wound will heal with no trouble.”

Despite his reassurance, you frown and touch the wound, but your annoyance is quickly dissipated as he continues to fuck you. You moan out again, adding to the noisy wet slaps of skin hitting skin that emanate from where the two of you are joined. There is no way that no one else is hearing this.

Your legs begin to tremble and you know you’re close to cumming again. Clarota takes hold of your knees, pushing them towards your shoulders. Thrusts becoming somewhat erratic, he manages to push his cock in even deeper at this position, balls hitting your ass, and his pubis presses against your clit.

“Fuck, Clarota… Clarota, I’m so close, I-I’m!” You throw your head back and writhe as wave after wave of bliss washes over you. He fucks your through your orgasm, adding to the pleasure. Clarota grunts harshly and slams his hips against yours, cock pulsing as thick ropes of his cum are released within you. He stills as a second pulse of his seed causes you to overflow.

Clarota pushes into you a few more times, extending the pleasure a little, before pulling out and taking the spot next to you.

The two of you lay in silence for a moment, basking in the afterglow, when you hear his voice in your mind.

“Initially, I would have chosen to eat Scanlan’s mind—I enjoy his songs,” he finally answers your question from earlier. “But now I believe I would choose yours, to be able to enjoy this moment from your point of view.”

“Aw, that’s…Kinda creepy, but sweet too.”

After another moment of relaxing, you redress and find your weapon. Now you have to take your shift as the guard seriously.

\----

Okay, guard duty was really boring. It’s been at least 3 hours and literally nothing has happened. Your eyes feel heavy and you swear that you fell asleep for a few seconds here and there, only for Clarota to shake you awake and scold you.

“Shit! I can’t even stay awake anymore! Is our shift over yet Clarota?”

“No, but our time is short,” his tentacles twitch in an irritated manner. “I suggest you find the willpower to stay awake for the remaining time.”

You saunter up to the Ilithid and pull him towards you by the hips. “How about we do something fun to pass the time?”

He huffs at your suggestion, but he can’t hide the stiffness in his trousers. You giggle and begin to undo your pants, shimmying them down your legs. Likewise, Clarota frees himself from his clothing and palms at his hardening cock.

You kneel on your fur pelt, inviting Clarota to take you from behind. You’re still very wet from your endeavors from just a few hours ago.

Clarota takes his spot behind you, taking a moment to admire your ass, rubbing and squeezing it, taking his cock and rubbing it along your pussy and crack.  He moans upon feeling your wetness on his member, quickly positioning himself and plunging his thick cock in fully.

“Ah, fuck! A little warning, maybe?” You say, despite already wanting him inside you. “Ah, hmm, that’s so good…. Clarota, fuck yes.” You moan as he continues to pound into you. You rest your forehead on your soft pelt, using one hand for support, the other now rubbing at your clit. The stimulation quickly brings you near orgasm. You slow the speed at which you’re touching yourself, not wanting to cum so quickly.

“Slowing down?” Clarota asks, beginning to fuck you harder and faster, and replaces your hand with his own on your clit.

“N-no, I don’t want to cum yet!” You protest, trying to hold back the inevitable. Breathing labored, you slam your hips back into Clarota’s, just a few hard pounds away from release….

And he pulls away.

“Wh-what are you doing? Why did you stop?” you glare sternly at him.

“You want to prolong this, yes? Then you will wait.” He says, slowly inserting two fingers, massaging your walls. It’s not enough to make you cum but it’s driving you crazy. You try to rub at your clit, but your hand is swiftly pulled away. “No, I decide when you cum, so be a good little human and obey me. Now get on top of me.”

He lays down and you straddle his hips, ready to plunge down onto his cock. “Now, ride me, but don’t cum.” You quickly insert him, moving up and down on his cock at a very pleasurable pace, quickly bringing yourself back to the near-orgasm level you were just at.  He grabs your hair and pulls your face near his, voice gruff now. “I said to not make yourself cum, you are not going to cum until I allow it.” He punctuates every other word by bucking up into you. “You will be severely punished.”

“S-stop, I’ll cum if you keep doing that!” you beg, trying to still his movements. He continues fucking you harshly, he wants you to cum, to break his rule. “Clarota! Clarota, I’m cumming! I’m sorry, I’m cumming, keep fucking me!” you lean your head against his shoulder and grind against him, wishing to feel his cock pulse with orgasm too, to be filled with his thick seed again.

“Tsk, how typical,” he pushes you off of him, “A disobedient little human that can’t play by the rules.” He positions you on your hands and knees, already pressing his fingers into your ass. They slip in with ease, massaging you in preparation from something much larger.

He doesn’t give you much warning before he’s already got the tip of his cock in, slowly filling you with the rest. You try to keep still under him, eyes screwed shut. The slick that was already on his cock acts like a lube, making it much easier for him to fuck your ass. The first thrust or two were uncomfortable as you adjusted to the sensation, but it quickly faded.

Clarota’s movements soon become erratic and he stills, cock twitching within you. You feel as his cum pulses into you several times before he pulls out.

You pout as he chuckles, ready to tell him off for fucking your ass with little lubrication, when you see movement not too far away.

“Oh my god,” Scanlan can barely talk, he’s laughing so much. He tries to ask you something but just keeps laughing.

“Scanlan! You’d better not tell anyone!” you threaten him as you attempt to redress yourself.

“Oh like hell I’m not!” he runs back into camp, laughing like a maniac. “Guys, wake up! You won’t BELIEVE…”

You cast invisibility on yourself and slink away, hoping to find safe passage out of the cave system, and to never see Vox Machina again.


End file.
